(2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid

• ChemBase ID: 176336
• Molecular Formular: C17H26N6O4
• Molecular Mass: 378.42614
• Monoisotopic Mass: 378.20155334
• SMILES: c1cn(c2c(c1)nc(n2)NCCC[C@H](N)C(=O)O)CCCC[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCCCn1cccc2c1nc(n2)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1
• InChIKey: AYEKKSTZQYEZPU-RYUDHWBXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid
• IUPAC Traditional name: pentosidine
• Synonyms: (αS)-α-Amino-2-[[(4S)-4-amino-4-carboxybutyl]amino]-4H-imidazo[4,5-b]pyridine-4-hexanoic Acid; [S-(R*,R*)]-α-Amino-2-[(4-amino-4-carboxybutyl)amino]-4H-Imidazo[4,5-b]pyridine-4-hexanoic Acid; Pentosidine

Database IDs

• CAS Number: 124505-87-9
• PubChem SID: 164232246
• PubChem CID: 119593

CALCULATED PROPERTIES

• Acid pKa: 1.5142641
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.8629222
• LogD (pH = 7.4): -3.8688157
• Log P: -3.8629823
• Molar Refractivity: 99.6063 cm^3
• Polarizability: 38.52628 Å^3
• Polar Surface Area: 169.38 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P276300

A biochemical marker of bone turnover for management of metabolic bone diseases.

REFERENCES

• Turner, W., et al.: Biol. Psychiatry, 14, 177 (1979)
• Miyata, T., et al.: Kidney Int., 60, 2351 (1979)
• Politi, P., et al.: Neurosci. Lett., 396, 163 (1979)